In the movie Office Space — a comedy about work life in a typical 1990s software company — the protagonist, Peter Gibbons, has eight different bosses. All of them, seemingly unaware of each other, pass by his desk and tell him what to do. While the film is most certainly a satire, for some, it is not far from the truth. More and more people report to more than one boss and learning to handle multiple managers is an essential skill in today’s complex organizations.

What the Experts Say
According to Robert Sutton, a professor of management science and engineering at Stanford University and the author of Good Boss, Bad Boss, it is extremely common these days to have more than one boss. “As you to go to a matrixed structure, you can easily have between one and seven immediate supervisors,” he says. Adam Grant, an associate professor at the University of Pennsylvania’s Wharton School and co-author of “The Hidden Advantages of Quiet Bosses,” concurs. “As companies continue to flatten, organize work around specific projects, and use temporary teams to complete projects, many employees find themselves reporting to multiple bosses,” he says. While this is more likely to happen in bigger and more complex organizations, it is just as common in start-ups and family-owned businesses. “In family-owned businesses authority structures are often blurry, and roles frequently overlap. As a result, employees can find themselves reporting to multiple members of the same family,” says Grant. Having many bosses is complicated and as Grant, who has worked for more than one boss at two different points in his career, says, “If you’re not careful, you can end up letting all of them down.” The first step is to know what you are up against. Then you can take several steps to mitigate the risks and make your job, and theirs, easier.

Recognize the challenges
Grant and Sutton agree that there are numerous challenges to working for more than one person. However, there are three main issues that you need to look out for:
Overload. With more than one person assigning you work, one of the greatest risks is simply having too much to do. “If you report to multiple bosses who supervise your efforts on different tasks and projects, it’s all too easy for each boss to treat you as if you have no other responsibilities,” says Grant.

Conflicting messages. “The more bosses you have the more conflicting messages you get,” says Sutton. He points out that sometimes this happens out of ignorance — your bosses aren’t aware of what the others are saying — or because people are pushing their own agendas. “Different bosses often have different expectations, and what impresses one may disappoint another,” says Grant. “When I led an advertising agency, I had an idea for expanding the agency’s imprint to new media. I brought it to both of my bosses. One loved it. The other hated it,” shares Grant.

Loyalty. “Some bosses want to know that they’re your first priority. If you have more than one boss who feels this way, it’s easy to get caught in the middle,” says Grant. Reporting to more than one person often requires you negotiate between competing demands for your loyalty.

You won’t necessarily face all three of these challenges, but knowing the most common ones can help you identify what you’re going through.

Know who your ultimate boss is
While you may have multiple managers you take direction from, most people have one person who is ultimately responsible for their career. When you enter a situation where you work for more than one person, be sure to ask a lot of questions about the reporting structure. Find out who completes your reviews, and who contributes to them. Ask who makes decisions about your compensation, promotions, etc. Sutton says that understanding who holds the most power will aid you in making decisions about how to act. While this may seem mercenary, it’s important to know from the outset who can help and hurt your career.

Be proactive about your workload
Be sure your bosses know what’s on your plate. While it may not be in your job description to negotiate between your bosses, it will behoove you. “I would err on the side of taking the initiative to coordinate between them. Research suggests that most bosses prefer proactive employees,” says Grant. You can create a shared document that lists all of your ongoing tasks and projects, or you can communicate these items in a weekly check-in meeting.

Get your bosses to communicate
Most bosses appreciate when you bring them solutions rather than problems. But this is complicated with more than one manager. Whether you need to resolve contradictory directions, reduce your workload, or sort out inconsistent demands, the best approach is to get your bosses to talk with each other, rather than trying to represent one’s agenda to the other. “Start by assuming the best. Invite them to discuss the conflicts and get it out on the table,” says Sutton. Bring your bosses together in the same place — in a conference room or on the same email chain — and explain what the conflict is. Enlist them in the problem solving and push for transparency. “If you ask your bosses for advice on how to handle the disagreement, they’re more likely to take your perspective and see the challenges from your point of view,” says Grant.

Set up boundaries
“The most important skill for staying sane while reporting to multiple bosses is the ability to set boundaries,” says Grant. He points to research done by Harvard Business School professor Leslie Perlow that shows the value of setting limits. Perlow found that engineers at a Fortune 500 company were constantly interrupted by managers and coworkers. She helped them create norms for quiet time: three days a week, there would be no interruptions before noon so they could focus on work. The engineers reported that these boundaries enhanced their productivity. If your multiple bosses frequently come to you with questions or to check in about their projects, establish protected times where you can be heads down without disruptions.

Get sneaky if you have to
The above advice works best in a healthy organization. But Sutton is quick to say that most organizations are not functional and yours may not reward transparency and being proactive. You may find that when conflicts arise between your bosses that they are unresponsive or unwilling to meet with you to resolve them. This requires a different approach. “If you’re in a fear-based environment, you have to figure out how to protect yourself. The worse the environment the more sneaky you have to get,” says Sutton. He suggests you figure out which of the bosses you work with has the most power and prioritize her assignments. “The smart employee doesn’t ask. Instead do your own calculation of who is more powerful and who would hurt you the least,” says Sutton. Understand the politics between your bosses and then make a thoughtful decision about whose request or demand to ignore.

Don’t take it personally
Sutton points out that it can be easy to develop paranoid fantasies about how your bosses are out to get you, but more likely than not, this is not the case. Chances are they are simply pushing their own agendas and you are getting caught in the middle. Try not to feel persecuted, but preemptively identify the conflicts and push to resolve them. In fact, having more than one boss can have benefits as well. Sutton says you are likely to have more autonomy than if you worked for one person. And you can more easily find ways to personalize your job. “Like a kid playing parents off each other, ask the person who you know will give you the answer you want,” says Sutton.

Principles to Remember

Do:
Be on the lookout for the most common challenges of having multiple bosses so you can proactively handle them
Keep a positive attitude and remember that the conflicts are most likely because of the situation, not because of you
Find out which of your bosses is responsible for making the decisions that affect your career

Don’t:
Try to speak on behalf of one boss to the other — try to get them to talk with each other if possible
Keep your workload and task list a secret from any of your bosses
Push for transparency if your organization doesn’t reward it

Case Study #1: A Monday morning to do list
Kim Bryant had been in the accounting industry for 15 years when she started with a new firm as a staff accountant. The company had three partners and Kim was initially hired to work under one of them. But soon she was asked to work for that partner and help out one of the others. “The most difficult thing about working for two partners was that both would have projects that they felt were urgent and it put me in an uncomfortable situation,” she says. Kim would have to try to decide which project to work on first. When she asked one of her bosses for advice, he would say he wanted his project done first. It was also not uncommon for one partner to assign her something urgent when she was working on an upcoming deadline for the other. To help coordinate between the two of them, she created a to do list every Monday morning, prioritized by due date, and shared it with the two partners. “That allowed each partner to be aware of what I had been assigned to do,” she says.

She also learned to watch their schedules, often with the help of the secretary. If Kim had been told that a project was urgent, she could gauge how soon she needed to do it based on when the partner was back in the office. She knew if she got it on his desk before he returned, she would be fine. “Communication and organization are critical,” she says. She also says a positive attitude helped her get through the conflicts.

Case Study #2: A balancing act
In his last job, Bob Tschetter reported to two people, one was his direct line manager, Susan*, and the other was a dotted line manager, Ross*. As a digital senior project manager, 100% of his time was allocated to the project owned by Ross. Yet, Susan completed his review, with input from Ross. Susan occasionally gave him extra work so he had to figure out how to manage the priorities and get it all done. Bob felt accountable to both managers and stayed at work progressively later in order to keep up with his increasing workload. He didn’t want to let either of them down and he felt it was worth it to put in extra time.

Bob also worked hard to establish a rapport with both managers so that he could go to them if and when conflicts arose. Early in the project, there was an issue with a vendor and Bob and Ross had differing views on how to handle it. Bob came up with a solution that integrated what both he and Ross wanted and involved others in the organization in deciding on the path forward. All the while, Bob kept Susan informed of the situation. He knew that since she was responsible for his review with input from Ross, he needed to keep them both happy. She praised him for influencing Ross’s decision, while also supporting Ross’s position. “The most important thing to remember is who completes the appraisal and who influences it. Once you know that, you know who to go to for help and support. The rest is a balancing act,” he says.